Divot

Derek Andersen
  • 5.0 (23)
  • Business
  • Updated Weekly

Divot brings you weekly conversations with the people building the future—founders, creators, athletes, and visionaries pushing the limits of business, technology, sports, and entertainment. We go beyond success stories to explore the real moments that define a journey—the risks, the failures, the breakthroughs, and the lessons that can help you on your path. Stories of people making their mark, and how you can too. New episodes every Wednesday. #DivotPodcast #Business #Tech #Sports #Entertainment #Innovation

  1. #53 Part 2: Charlie Rocket on Manifesting Backwards, Winning Streaks & Making Impossible Dreams Real

    10h ago

    #53 Part 2: Charlie Rocket on Manifesting Backwards, Winning Streaks & Making Impossible Dreams Real

    Charlie Rocket believes your dream may already be done; time just has not caught up yet. In Part 2 of this conversation, the Dream Machine Foundation founder explains how the things that light you up can become a signal, a direction, and a reason to move before the world gives you proof. In this episode with Derek Andersen, Charlie breaks down manifesting backwards, speaking the future before it exists, and building a winning streak in your mind. He shares why he walked away from a $15M business to chase becoming a Nike athlete, how writing things down makes the invisible feel real, and why words can shape the reality you move toward. The conversation goes deeper into dreams, miracles, faith, identity, and the courage to live inside possibility. Charlie shows that life can change faster than most people think when you stop waiting for certainty and start acting from the future you believe is already on the way. Follow Charlie - Instagram: https://www.instagram.com/charlieFollow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners:Google for StartupsGrab the new Google for Startups Future of AI report at https://goo.gle/futureofgenmedia Timestamps:01:32 — How to Find the Dream That Lights You Up05:06 — Why Charlie Walked Away From a $15M Business06:01 — How to Manifest Backwards11:37 — Speaking the Future Before It Exists15:53 — Charlie’s Nike Manifestation Story17:19 — Why Writing Things Down Makes Dreams Real19:28 — How to Start Seeing Miracles22:23 — Derek’s Scotty Cameron Miracle Story27:15 — You Weren’t Derailed, You Were Delivered28:11 — The Pain That Built Charlie’s Success36:25 — The Winning Streak That Changed His Life37:35 — How to Overcome Hard Things38:57 — Measuring Life in Possibilities39:53 — What Charlie Hopes God Says Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#charlierocket #delusionaloptimism #manifestingbackwards #winningstreak #impossibledreams #dreammachine #manifestation #mindset #personalgrowth #reinvention #miracles #purpose #possibility #entrepreneurship #divotpodcast

    40 min
  2. #53: Brain Tumor, Losing 120 Pounds & Becoming a Nike Athlete: Charlie’s Delusional Optimism Formula

    Jun 10

    #53: Brain Tumor, Losing 120 Pounds & Becoming a Nike Athlete: Charlie’s Delusional Optimism Formula

    Charlie Rocket helped create major cultural moments in hip hop, working with artists like 2 Chainz, contributing to Grammy-winning campaigns, winning an Emmy, and managing some of the biggest names in music. But after facing obesity, depression, burnout, and a brain tumor, Charlie reinvented everything: he lost 120 pounds, became a Nike athlete, ran across America, and turned Dream Machine Foundation into a global movement for impossible dreams. In this episode with Derek Andersen, Charlie breaks down his Delusional Optimism Formula: how to turn pain into proof, proof into belief, and belief into action. He explains why the key to changing your life is building a winning streak in your mind, collecting constant proof that you are winning, and training yourself to see setbacks, rejection, and failure as signs that life is still working for you. The conversation goes deeper into reinvention, identity, manifestation, gratitude, viral content, and the courage to believe your life can change faster than you think. Charlie shows that impossible dreams are not built by avoiding pain. They are built by turning every loss into momentum, every setback into a lesson, and every small win into proof that your dream is already on the way. Follow Charlie - Instagram: https://www.instagram.com/charlieFollow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners:Google for StartupsGrab the new Google for Startups Future of AI report at https://goo.gle/futureofgenmedia Timestamps:00:00 — Charlie Rocket’s Delusional Optimism Formula00:36 — From Hip Hop Success to a Life-Changing Brain Tumor00:56 — Losing 120 Pounds and Becoming a Nike Athlete05:08 — Why You Are Undefeated09:28 — Turning Every Loss Into a Win12:37 — What Delusional Optimism Really Means17:33 — Proof Creates Delusion, Delusion Creates Action30:02 — How to Become a Delusional Optimist34:59 — How to Reinvent Yourself35:33 — Kobe Bryant, Black Mamba, and the Alter Ego Effect40:57 — Charlie’s Viral Content System42:16 — 20M Views and 200K Followers in 45 Days44:43 — How to Build a Winning Streak Every Morning57:48 — How Fast Your Life Can Change Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#charlierocket #delusionaloptimism #nikeathlete #dreammachine #reinvention #mindset #manifestation #winningstreak #personalgrowth #impossibledreams #brainTumorSurvivor #entrepreneurship #founderjourney #motivation #divotpodcast

    1h 1m
  3. #52: He Built a 22M Media Empire by Interviewing Tom Cruise, Shaq, Brady & 52 Billionaires

    Jun 3

    #52: He Built a 22M Media Empire by Interviewing Tom Cruise, Shaq, Brady & 52 Billionaires

    James Dumoulin built School of Hard Knocks into a 22M-follower business media empire by turning street interviews into a new form of financial education. By 23, he had interviewed 52 billionaires and major icons like Tom Cruise, Tom Brady, and Shaquille O’Neal, after once posting hundreds of times with almost no audience. In this episode with Derek Andersen, James breaks down the creator economy, the pivot that changed everything, and how he mastered organic content, watch time, hooks, and distribution. He explains why the first 3 seconds decide whether a video survives, why quantity creates quality, and how founders can use content to build real business leverage. The conversation goes deeper into rejection, courage, and credibility, from asking Mark Cuban for his first billionaire interview to scaling toward one of the biggest business media networks in the world. James shows what it really takes to earn attention before anyone gives you permission. Follow James - Instagram: https://www.instagram.com/realjamesdumoulinFollow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners:Google for StartupsGrab the new Google for Startups Future of AI report at https://goo.gle/futureofgenmedia Timestamps:01:48 — How School of Hard Knocks Started03:56 — 400 Posts With Only 50 Followers04:41 — From $100K Months to $1M Months06:15 — How Small Teams Can Win With Content09:24 — The Only Metric That Matters Online10:20 — Why the First 3 Seconds Decide Everything13:03 — How Travel Shaped James’ Ambition14:25 — Turning Rejection Into Fuel15:41 — Interviewing 52 Billionaires by 2315:52 — How James Got Mark Cuban17:30 — Tom Cruise, Brady, Shaq, and Bigger Asks20:08 — Why Business Takes Courage20:50 — Building One of the Biggest Business Media Networks Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#jamesdumoulin #schoolofhardknocks #contentcreation #goingviral #watchtime #entrepreneurship #businessmedia #founderjourney #creatoreconomy #divotpodcast

    23 min
  4. #51: Justin Kan on Success, Happiness & Why Achievement Never Feels Enough | Twitch Founder

    May 28

    #51: Justin Kan on Success, Happiness & Why Achievement Never Feels Enough | Twitch Founder

    Justin Kan helped build Twitch into one of the most influential companies in internet history, changing gaming, streaming, and creator culture forever. After selling the company for nearly $1 billion to Amazon, becoming one of Silicon Valley’s most recognizable entrepreneurs and investors, Justin realized something uncomfortable: achievement alone does not create fulfillment. In this episode with Derek Andersen, Twitch co-founder Justin Kan breaks down the hidden psychology behind ambition, money, status, comparison, and happiness. He explains why success quickly becomes your new baseline, why social media quietly destroys mental health, how gratitude journaling completely rewired his brain, and why many founders spend their lives chasing goals that never truly satisfy them. The conversation goes deeper into identity, self-worth, and the emotional cost of ambition, why intrinsic motivation matters more than external validation, the traits Justin looks for in great founders, and why the next generation should build where nobody is looking yet. Follow Justin - X (Twitter): https://x.com/justinkanFollow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners:Google for StartupsGrab the new Google for Startups Future of AI report at https://goo.gle/futureofgenmedia Timestamps:01:40 — Justin Kan’s Tattoo About Gratitude02:46 — Why Success Still Creates Comparison03:36 — Why Money and Fame Don’t Create Happiness06:55 — Why Achievement Only Feels Good for a Moment10:51 — The Habit That Rewired Justin’s Brain16:39 — AI, Mental Health, and Social Media18:10 — Why Justin Isn’t Chasing the AI Gold Rush21:49 — The Founder Trait Justin Looks For Most23:19 — Why Justin Invested $8 Million After a Cold Plunge26:20 — Why You Shouldn’t Chase the AI Crowd26:44 — The Next Big Frontier After AI Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#justinkan #twitch #siliconvalley #entrepreneurship #startupfounder #mentalhealth #successmindset #founderjourney #personalgrowth #divotpodcast

    28 min
  5. #50: Claude, AI Agents & the End of Traditional SaaS | Navin Chaddha

    May 20

    #50: Claude, AI Agents & the End of Traditional SaaS | Navin Chaddha

    Navin Chaddha is the Managing Partner of Mayfield, one of Silicon Valley’s most legendary venture capital firms with over $3B under management and more than 120 IPOs. A 17-time Forbes Midas List investor, Navin was an early backer of companies like Lyft, HashiCorp, Poshmark, SolarCity, and Nuvia, which sold to Qualcomm for $1.4B. In this episode with Derek Andersen, Navin Chaddha breaks down why AI may become a bigger technological shift than the internet, why tools like Claude are changing software engineering forever, and why AI agents could replace many traditional SaaS workflows. He explains how companies like Nvidia, OpenAI, and Anthropic are building the new “intelligence grid,” why infrastructure wins first in every major technology revolution, and where founders should focus as AI-native startups begin disrupting entire industries. Navin also shares why founders who embrace AI-native thinking early may gain one of the biggest advantages of the next decade, while incumbents that resist the shift risk being left behind. Follow Navin- X (Twitter): https://x.com/NavinChaddha Follow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners: Google for Startups Grab the new Google for Startups Future of AI report at https://goo.gle/futureofgenmedia Timestamps: 01:14 — Why AI Is a “100x Force” for Humanity 02:27 — Where the Biggest Value in AI Is Being Created 04:19 — Nvidia, Infrastructure & the AI Gold Rush 06:02 — The Next Massive Opportunities Beyond Compute 08:03 — Why Claude Changed Software Engineering 10:05 — Claude as the “New Browser for Work” 12:31 — AI Agents & the End of Traditional SaaS 15:08 — The Rise of Headless Software Explained 18:12 — Why Everyone Can Now Become a Builder 21:05 — Human + AI Teams Will Replace Old Workflows 23:16 — Navin Chaddha’s Biggest Advice for Founders Follow Divot: YouTube: https://www.youtube.com/@Divotpod X (Twitter): https://twitter.com/divotdotorg Instagram: https://www.instagram.com/divotpod TikTok: https://www.tiktok.com/@divotpod LinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags: #aiagents #claudeai #artificialintelligence #futureofwork #openai #anthropic #saas #navinchaddha #nvidia #machinelearning #futureofsoftware #startupfounders #techpodcast #airevolution #siliconvalley #automation #founderjourney #venturecapital #aiinnovation #divotpodcast

    28 min
  6. #49: Success, Loneliness, Ambition & Why High Performers Never Feel Enough | David Spinks

    May 13

    #49: Success, Loneliness, Ambition & Why High Performers Never Feel Enough | David Spinks

    David Spinks spent years building one of the most respected communities in Silicon Valley, co-founding CMX, advising top companies on belonging, and helping define an entire industry around community building. But beneath the success, achievement, and ambition, he still felt empty. In this episode with Derek Andersen, David Spinks breaks down the hidden emotional cost of high performance, why so many ambitious people struggle with loneliness, burnout, self-worth, and fulfillment, and why success alone never creates lasting happiness. He explains the dangerous relationship between ambition and identity, the loneliness epidemic affecting modern society, why high achievers often never feel “good enough,” and how startup culture conditions people to tie their worth to achievement, productivity, and external validation. The conversation goes deeper into belonging, emotional safety, purpose, fatherhood, mental health, Silicon Valley culture, spirituality, enoughness, and what it actually means to build a meaningful life without sacrificing your well-being, relationships, and inner peace. Follow David - Instagram: https://x.com/DavidSpinksFollow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners:Google for StartupsGrab the new Google for Startups Future of AI report at https://goo.gle/futureofgenmedia Timestamps:03:11 — What Community & Belonging Really Mean04:34 — The Loneliness Epidemic & Social Media Addiction06:40 — What It Truly Means to Feel Like You Belong12:33 — Can Businesses Ever Replace Real Community?15:39 — How Communities Mirror Human Nature & Leadership19:40 — Silicon Valley, Success & the Need to Prove Yourself23:51 — Why Success Never Makes You Feel “Enough”24:19 — The False Tradeoff Between Ambition & Happiness28:00 — Elon Musk, Steve Jobs & the Price of Greatness31:37 — Is Making a Dent in the Universe Worth the Cost?36:20 — Why “Saving the World” Often Starts at Home41:04 — The Hardest Lesson: You Are Already Enough44:22 — The One Idea David Wishes Everyone Believed45:19 — Best Advice for Overcoming Fear & Hard Things46:03 — Fatherhood, Presence & What Really Matters47:27 — Why Measuring Your Life Can Be Dangerous Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#successmindset #highachievers #selfworth #ambition #loneliness #mentalhealth #personalgrowth #burnout #foundermindset #divotpodcast

    49 min
  7. #48: Wiz, Datadog & The Mindset Behind Billion Dollar Companies | Shardul Shah Index Ventures

    May 6

    #48: Wiz, Datadog & The Mindset Behind Billion Dollar Companies | Shardul Shah Index Ventures

    Shardul Shah has backed some of the most important technology companies of the last decade. From Datadog to Wiz, his investments have helped shape the future of cybersecurity, cloud infrastructure, artificial intelligence, and enterprise software. In this episode, Derek Andersen, Shardul Shah, partner at Index Ventures, breaks down the mindset behind billion-dollar startups, how elite founders think about AI, venture capital, acquisitions, intuition, ambition, and building category-defining companies. He explains why most startup founders misunderstand venture capital, why imagination matters as much as execution, and the two questions every entrepreneur must answer before selling their company. The conversation goes deeper into trust, relationships, founder psychology, ego, and purpose, why the best investors study people more than markets, how intuition shapes billion-dollar decisions, and what separates iconic founders from short-term operators. Plus, the untold stories behind Wiz’s $32 billion acquisition, Datadog’s early days, Michael Jordan’s influence on competition, Nas, Dave Chappelle, and the investing philosophy behind some of the most successful startup outcomes of the last decade. Follow Sahil - Instagram: https://x.com/shardul_shahFollow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners:Google for StartupsGrab the new Google for Startups Future of AI report at https://goo.gle/futureofgenmedia Timestamps:02:43 — How a Random Encounter Changed His Entire Life05:16 — Why Great Startup Founders Can Come From Anywhere08:06 — Why Shardul Refuses to Invest Over Zoom13:32 — Why Engineers Are Being Measured By Token Usage14:39 — The Trait Every Billion Dollar Founder Shares20:09 — The Brutal Truth About Boardroom Disagreements24:03 — How Building Communities Led To Billion Dollar Companies27:11 — Why Datadog Looked Like a Terrible Investment29:03 — The Mindset Required To Invest Before Everyone Else33:29 — Inside Wiz’s Historic $32 Billion Acquisition35:40 — The 2 Questions Every Founder Must Answer36:24 — If You Can 10X Your Company, Never Sell40:17 — The Difference Between Your Heart & Your Mind42:00 — The Ancient Philosophy That Changed How He Thinks49:34 — Why Michael Jordan Obsessed Him With Competition52:23 — Dave Chappelle, Nas & The Best Night of His Life54:00 — The Truth About Intuition & Great Decisions Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#shardulshah #wiz #datadog #venturecapital #startupfounders #artificialintelligence #cybersecurity #foundermindset #entrepreneurmindset #divotpodcast

    56 min
  8. #47: The 5 Types of Wealth & Why You’re Chasing the Wrong One | Sahil Bloom

    Apr 29

    #47: The 5 Types of Wealth & Why You’re Chasing the Wrong One | Sahil Bloom

    Sahil Bloom grew up with one scoreboard: money. He worked his way into top private equity firms, built a career most would envy, and still felt hollow, until he started questioning what wealth actually means. In this episode with Derek Andersen, Sahil Bloom, NYT bestselling author of The Five Types of Wealth, breaks down the framework redefining how millions think about success, time wealth, social wealth, mental wealth, physical wealth, and financial wealth. He explains the arrival fallacy that traps high achievers, why ambition without direction destroys more lives than failure ever could, and how building a "margin of freedom" early determines whether you'll ever actually escape the golden cage. The episode goes deeper into identity, purpose, and what a good life actually looks like, why your quest matters more than your goals, how to stop living by someone else's design, and the one conversation with his wife that changed everything. Follow Sahil - Instagram: https://x.com/SahilBloomFollow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners:Google for StartupsGrab the new Google for Startups Future of AI report at https://g.co/futureofgenmedia Timestamps:01:05 — The 5 Types of Wealth That Actually Matter02:09 — Why Chasing Money Leads You Off a Cliff05:16 — Why Success Feels Empty After You Achieve It07:16 — You’ll Always Want More Money (Here’s Why)11:40 — Humans Need a Quest to Feel Alive16:19 — Ambition Without Direction Is Miserable18:21 — Direction not Speed (The Life Rule That Matters)20:15 — Why People Stay Stuck in “Good Enough” Lives27:27 — How to Actually Change Your Life28:25 — The Danger of Winning the Wrong Game50:16 — What Real Confidence Actually Means58:35 — The Best Advice for Doing Hard Things Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#5typesofwealth #sahilbloom #wealthmindset #founderjourney #entrepreneurmindset #purposedriven #timewealth #buildingmeaningfullife #personalgrowth #divotpodcast

    1h 2m
See All (55)

5
out of 5
23 Ratings

About

Divot brings you weekly conversations with the people building the future—founders, creators, athletes, and visionaries pushing the limits of business, technology, sports, and entertainment. We go beyond success stories to explore the real moments that define a journey—the risks, the failures, the breakthroughs, and the lessons that can help you on your path. Stories of people making their mark, and how you can too. New episodes every Wednesday. #DivotPodcast #Business #Tech #Sports #Entertainment #Innovation

Information

  • Creator
    Derek Andersen
  • Years Active
    2025 - 2026
  • Episodes
    55
  • Rating
    Clean
  • Copyright
    © Derek Andersen
  • Show Website
    Divot

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